Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX

Journal of the American Chemical Society

Volumn 128, Issue 25, 2006, Pages 8329-8335

  Alterio, Vincenzo ^a   Vitale, Rosa Maria ^a   Monti, Simona Maria ^a   Pedone, Carlo ^a,b   Scozzafava, Andrea ^c   Cecchi, Alessandro ^c   De Simone, Giuseppina ^a   Supuran, Claudiu T ^c  

^a CNR   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; COMPLEXATION; FLUORESCENCE; HYDROGEN BONDS; MATHEMATICAL MODELS; TUMORS;

BENZESULFONAMIDES; CARBONIC ANHYDRASE INHIBITORS; FLUORESCENT ANTITUMOR SULFONAMIDE;

ENZYME INHIBITION;

ANTINEOPLASTIC AGENT; BENZENESULFONAMIDE DERIVATIVE; CARBONATE DEHYDRATASE INHIBITOR; FLUORESCEIN; GLUTAMIC ACID; GLUTAMINE; GUANIDINE; ISOENZYME; LEUCINE; PHENYLALANINE; PROLINE; SULFONAMIDE; THREONINE; VALINE; ZINC ION;

ARTICLE; CRYSTAL STRUCTURE; ENZYME ACTIVE SITE; HYDROGEN BOND; IONIZATION; MOLECULAR MODEL; TUMOR; X RAY;

AMINO ACID SEQUENCE; ANTIGENS, NEOPLASM; ANTINEOPLASTIC AGENTS; BINDING SITES; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; FLUORESCEINS; FLUORESCENCE; ISOENZYMES; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; SEQUENCE ALIGNMENT; SPECTROMETRY, FLUORESCENCE; SULFONAMIDES; THIOUREA;

EID: 33745644458     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja061574s     Document Type: Article

References (49)

1. Pastorekova, S.; Parkkila, S.; Pastorek, J.; Supuran, C. T. J. Enzyme Inhib. Med. Chem. 2004, 19, 199-229.
2. Lehtonen, J.; Shen, B.; Vihinen, M.; Casini, A.; Scozzafava, A.; Supuran, C. T.; Parkkila, A. K.; Saarnio, J.; Kivela, A. J.; Waheed, A.; Sly, W. S.; Parkkila, S. J. Biol. Chem. 2004, 279, 2719-2727.
3. Supuran, C. T.; Scozzafava, A.; Casini, A. Med. Res. Rev. 2003, 23, 146-189.
4. Supuran, C. T.; Vullo, D.; Manole, G.; Casini, A.; Scozzafava, A. Curr. Med. Chem. Cardiovasc. Hematol. Agents 2004, 2, 49-68.
5. Tashian, R. E.; Venta, P. J.; Nicewander, P. H.; Hewett-Emmett, D. Prog. Clin. Biol. Res. 1990, 344, 159-175.
6. Fujikawa-Adachi, K.; Nishimori, I.; Taguchi, T.; Onishi, S. J. Biol. Chem. 1999, 274, 21228-21233.
7. Nishimori, I.; Onishi, S. Dig. Liver Dis. 2001, 33, 68-74.
8. Marquis, R. E.; Whitson, J. T. Drugs Aging 2005, 22, 1-21.
9. Vullo, D.; Innocenti, A.; Nishimori, I.; Pastorek, J.; Scozzafava, A.; Pastorekova, S.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2005, 15, 963-969.
10. Santos, M. A.; Marques, S.; Gil, M.; Tegoni, M.; Seozzafava, A.; Supuran, C. T. J. Enzyme Inhib. Med. Chem. 2003, 18, 233-242.
11. Loiselle, F. B.; Morgan, P. E.; Alvarez, B. V.; Casey, J. R. Am. J. Physiol. Cell Physiol. 2004, 286, C1423-1433.
12. Rivera, C.; Voipio, J.; Kaila, K. J. Physiol. 2005, 562, 27-36.
13. Vullo, D.; Voipio, J.; Innocenti, A.; Rivera, C.; Ranki, H.; Scozzafava, A.; Kaila, K.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2005, 15, 971-976.
14. Lyons, K. E.; Pahwa, R.; Comella, C. L.; Eisa, M. S.; Elble, R. J.; Fahn, S.; Jankovic, J.; Juncos, J. L.; Koller, W. C.; Ondo, W. G.; Sethi, K. D.; Stern, M. B.; Tanner, C. M.; Tintner, R.; Watts, R. L. Drug Saf. 2003, 26, 461-481.
15. Garske, L. A.; Brown, M. G.; Morrison, S. C. J. Appl. Physiol. 2003, 94, 991-996.
16. Hori, K.; Ishida, S.; Inoue, M.; Shinoda, K.; Kawashima, S.; Kitamura, S.; Oguchi, Y. Retina 2004, 24, 481-482.
17. Winum, J. Y.; Scozzafava, A.; Montero, J. L.; Supuran, C. T. Med. Res. Rev. 2005, 25, 186-228.
18. Supuran, C. T. Expert Opinion on Therapeutic Patents 2003, 13, 1545-1550.
19. Svastova, E.; Hulikova, A.; Rafajova, M.; Zat'ovicova, M.; Gibadulinova, A.; Casini, A.; Cecchi, A.; Suozzafava, A.; Supuran, C. T.; Pastorek, J.; Pastorekova, S. FEBS Lett. 2004, 577, 439-445.
20. Cecchi, A.; Hulikova, A.; Pastorek, J.; Pastorekova, S.; Scozzafava, A.; Winum, J. Y.; Montero, J. L.; Supuran, C. T. J. Med. Chem. 2005, 48, 4834-4841.
21. Elbaum, D.; Nair, S. K.; Patchan, M. W.; Thompson, R. B.; Christianson, D. W. Journal of the American Chemical Society 1996, 118, 8381-8387.
22. Eriksson, A. E.; Jones, T. A.; Liljas, A. Proteins 1988, 4, 274-282.
23. Brunger, A. T.; Adams, P. D.; Clore, G. M.; DeLano, W. L.; Gros, P.; Grosse-Kunstleve, R. W.; Jiang, J. S.; Kuszewski, J.; Nilges, M.; Pannu, N. S.; Read, R. J.; Rice, L. M.; Simonson, T.; Warren, G. L. Acta Crystallogr., Sect. D 1998, 54 (Pt 5), 905-921.
24. Abbate, F.; Supuran, C. T.; Scozzafava, A.; Orioli, P.; Stubbs, M. T.; Klebe, G. J. Med. Chem. 2002, 45, 3583-3587.
25. Abbate, F.; Casini, A.; Owa, T.; Scozzafava, A.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2004, 14, 217-223.
26. Abbate, F.; Winum, J. Y.; Potter, B. V.; Casini, A.; Montero, J. L.; Scozzafava, A.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2004, 14, 231-234.
27. Weber, A.; Casini, A.; Heine, A.; Kuhn, D.; Supuran, C. T.; Scozzafava, A.; Klebe, G. J. Med. Chem. 2004, 47, 550-557.
28. Abbate, F.; Casini, A.; Scozzafava, A.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2004, 14, 2357-2361.
29. Abbate, F.; Coetzee, A.; Casini, A.; Ciattini, S.; Scozzafava, A.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2004, 14, 337-341.
30. Di Fiore, A.; De Simone, G.; Menchise, V.; Pedone, C.; Casini, A.; Scozzafava, A.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2005, 15, 1937-1942.
31. Menchise, V.; De Simone, G.; Alterio, V.; Di Fiore, A.; Pedone, C.; Scozzafava, A.; Supuran, C. T. J. Med. Chem. 2005, 48, 5721-5727.
32. Whittington, D. A.; Grubb, J. H.; Waheed, A.; Shah, G. N.; Sly, W. S.; Christianson, D. W. J. Biol. Chem. 2004, 279, 7223-7228.
33. Stams, T.; Christianson, D. W. EXS 2000, 159-174.
34. Otwinowski, Z.; Minor, W. Methods in Enzymology 1997, 276, 307-326.
35. Jones, T. A.; Zou, J. Y.; Cowan, S. W.; Kjeldgaard Acta Crystallogr., Sect. A 1991, 47 (Pt 2), 110-119.
36. Laskowski, R. A.; MacArthur, M. W.; Moss, D. S.; Thornton, J. M. Journal of Applied Crystallography 1993, 26, 283-291.
37. Boeckmann, B.; Bairoch, A.; Apweiler, R.; Blatter, M. C.; Estreicher, A.; Gasteiger, E.; Martin, M. J.; Michoud, K.; O'Donovan, C.; Phan, I.; Pilbout, S.; Schneider, M. Nucleic Acids Res. 2003, 31, 365-370.
38. Altschul, S. F.; Madden, T. L.; Schaffer, A. A.; Zhang, J.; Zhang, Z.; Miller, W.; Lipman, D. J. Nucleic Acids Res. 1997, 25, 3389-3402.
39. Thompson, J. D.; Higgins, D. G.; Gibson, T. J. Nucleic Acids Res. 1994, 22, 4673-4680.
40. Sali, A.; Blundell, T. L. J. Mol. Biol. 1993, 234, 779-815.
41. Bowie, J. U.; Luthy, R.; Eisenberg, D. Science 1991, 253, 164-170.
42. Pearlman, D. A.; Case, D. A.; Caldwell, J. W.; Ross, W. S.; Cheatham, T. E., III; DeBolt, S.; Ferguson, D.; Seibel, G.; Kollman, P. Computer Physics Communications 1995, 91, 1-42.
43. Wang, J.; Cieplak, P.; Kollman, P. A. Journal of Computational Chemistry 2000, 21, 1049-1074.
44. Bayly, C. I.; Cieplak, P.; Cornell, W.; Kollman, P. A. Journal of Physical Chemistry 1993, 97, 10269-10280.
45. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery J. A. Journal of Computational Chemistry 1993, 14, 1347-1363.
46. Suarez, D.; Merz, K. M., Jr. J. Am. Chem. Soc. 2001, 123, 3759-3770.
47. Hoops, S. C.; Anderson, K. W.; Merz, K. M., Jr. Journal of the American Chemical Society 1991, 113, 8262-8270.
48. Ryckaert, J. P.; Ciccotti, G.; Berendsen, H. J. C. Journal of Computational Physics 1977, 23, 327-341.
49. Koradi, R.; Billeter, M.; Wuethrich, K. Journal of Molecular Graphics 1996, 14, 51-55. plates, 29-32.